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Open Access Conformational Study and Chiroptical Properties of Chiral Dimethyl-Ethylenedithio-Tetrathiafulvalene (DM-EDT-TTF)

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The enantiopure dimethyl-ethylenedithio-tetrathiafulvalene (DM-EDT-TTF) donor exists as biaxial (ax, ax) and biequatorial (eq, eq) conformers in equilibrium. DFT calculations combined with free energy surface (FES) analysis establish that the (ax, ax) form is more stable by ∼0.7 kcal·mol–1 than the (eq, eq) one and that the inter-conversion process involves a sequential conformational change through a boat type (ax, eq) conformer with an activation energy of ∼3 kcal.mol–1. TD-DFT calculations show similar, but opposite in sign, CD bands for the two conformers. A Boltzmann type average of the two CD curves, corresponding to a ratio of three (ax, ax) for one (eq, eq) conformers in equilibrium in solution, provides an excellent agreement with the experimental curve.

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Keywords: CHIRALITY; CIRCULAR DICHROISM; DFT CALCULATIONS; FREE ENERGY SURFACE ANALYSIS; TETRATHIAFULVALENES

Document Type: Research Article

Affiliations: 1: Laboratoire Moltech-Anjou, UMR 6200 CNRS- Université d'Angers, UFR Sciences, Bât. K 2 Bd. Lavoisier, 49045 Angers, France;, Email: [email protected] 2: Laboratoire Moltech-Anjou, UMR 6200 CNRS-Université d'Angers, UFR Sciences, Bât. K 2 Bd. Lavoisier, 49045 Angers, France 3: Laboratoire de Chimie et Physique Quantiques LCPQ/IRSAMC Université de Toulouse (UPS) and CNRS 118 Route de Narbonne, F-31062 Toulouse, France 4: Laboratoire Moltech-Anjou, UMR 6200 CNRS-Université d'Angers, UFR Sciences, Bât. K 2 Bd. Lavoisier, 49045 Angers, France;, Email: [email protected]

Publication date: June 1, 2018

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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